Ideally I would talk to Monahan near the trade deadline, this allows both the team and player to have more time to evaluate things, Hugo can than talk openly about how they see things moving forward contract wise, and Monahan has a better perspective regarding making Montreal home for up to 5 years, part of the negotiations could involve a ready to sign contract in a drawer to be pulled out at free agency, or test the market and come back to us, but i think Monahan would be ok with a playoff run with a contender if the habs are falling short come trade deadline,it would allow the habs to get more picks/prospects and Monahan may want to get traded to a team in the other conference hoping to play against the Flames. also you do not insult the guy with a contract offer making less than dvorak and Dach, 5 years at 5 million per is a bargain, for what he delivers, it is worth offering even if he goes on LTIR at some point, remembering that the cap is going up, plus what do players like him command salary wise.